Kimberly Guilfoyle Outfits That Prove Don Jr.'s Reported Style Criticism Didn't Faze Her

As if being suddenly disconnected from the president's family weren't awful enough, the reported reason Donald Trump Jr. ditched Kimberly Guilfoyle for his mistress was beyond humiliating. According to anonymous (aren't they all?) sources who dished to People, the oldest First Son strayed toward socialite Bettina Anderson because she has a more understated and — dare we say it? — classier style than the former Fox News host. This, in turn, makes better optics when he attends President Donald Trump's social events, such as his glammed-to-the-max New Year's Eve party at Mar-a-Lago. Explaining that Guilfoyle "never looks relaxed or casual" in her towering stilettos and micro-minis, one of the sources said, "The tight dresses need to go, and she has been told that."

Maybe she didn't get the memo. With only rare exceptions, Guilfoyle is still stepping out in leg- and cleavage-baring frocks that are anything but conservative. Is it a defiant "You can't tell me how to dress!" slap at her ex, or does she truly feel her best when she's pushing the envelope of modesty? Possibly she's still rebelling against her days as a courtroom attorney and first lady of California, when her wardrobe was expected to be more understated. Whatever the reason, Guilfoyle doesn't seem interested in changing her aesthetic. She's certainly had plenty of post-breakup looks that prove the point.

Kimberly Guilfoyle has gone Barbiecore quite often, but alas, her love of tiny dresses and unfortunate detailing tends to cheapen the look. It happened yet again on February 19, 2025, at the annual Old Bags Luncheon, a charity event in which the Palm Beach élite bid on designer handbags to raise money for a local family behavioral health center. In all fairness, Guilfoyle didn't look totally out of place; flashy prints and tropical colors were everywhere. But the tight fit and short hemline are the kind of style that was supposedly a turn-off for Don Jr. It would have been nice to have seen Guilfoyle in a pantsuit like the one seen here on Alana Stewart, the actress-model who personifies timeless beauty. 

"The dream team" was how Kimberly Guilfoyle captioned this photo from a recent undated event. She posed with three of President Trump's favorite cabinet members: FBI director Kash Patel; Richard Grenell, interim director of the Kennedy Center; and Trump's legal counselor, Alina Habba. It seemed an odd description, considering the four are working in very different areas of the administration. But the true oddity in the photo was Guilfoyle's choice of outfit. Her too-tiny dress, featuring a neckline that plunged nearly down to her hair extensions, hardly seemed appropriate for a grouping of government officials.

Kimberly Guilfoyle and Kash Patel rubbed elbows yet again, this time with actor-producer Eduardo Verástegui at a February 2025 CPAC event. And speaking of repeating, Guilfoyle sported the same tired style she often turns to at fundraisers and other 'dos. She favors dresses with bow detailing, either on the sleeves or on the bodice, as was the case here. Not that there's anything wrong with a signature accessory; the late Queen Elizabeth was almost never seen without a string of pearls, for instance. But multiple bows just tend to scream "middle-school prom," not "U.S. ambassador to Greece."

If anyone had any doubts about Kimberly Guilfoyle not being able to look "relaxed and casual," her appearance at Super Bowl LXI should put those doubts to rest. If ever there were a time to hang out in a team jersey and jeans, this was it; instead, the controversial conservative showed up to the VIP area in skintight red leggings, thigh-high boots, and a fur shrug. Posing next to photographer and Chiefs fan Austin Ryde, she looked as though she'd gone to the wrong event. The only person who looked more out of place at the big game was Ivanka Trump, whose white pantsuit was definitely not made for wings and beer.